


Brady's Matchmaking

by Crows Oneshots (CrowNoYami)



Series: Earned [1]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, M/M, Oral Sex, Smut
Language: English
Status: Completed
Published: 2017-06-02
Updated: 2017-06-02
Packaged: 2018-11-08 03:27:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,212
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11073096
Author URL: https://archiveofourown.org/users/CrowNoYami/pseuds/Crows%20Oneshots
Summary: Sam had been avoiding going to parties, he had other things he needed to do, assignments that needed done. When Brady eventually convinces him to go to one, to meet the perfect match for him, Jess, Sam instead finds himself trapped in whiskey eyes and a cocky grin. While he hadn't been looking to hook up until he knew for sure his past was behind him there was something about those eyes that pulled him in, and for once he was glad he was lost.





	Brady's Matchmaking

**Author's Note:**

  * For [NavajoLovesDestiel](https://archiveofourown.org/users/NavajoLovesDestiel/gifts).



> Authors note: Now that I've finished both Stanford Art and Death's Angel I'm back writing this. I'll be editing this week and will begin writing new chapters next week. Season Premier Tonight!!! 
> 
> Warnings: Slash, what might be seen as Jess!Bashing, anal sex, oral sex, anal fingering. 
> 
> **edited 10/12/2017

 

**Brady’s Matchmaking**

"I need to have this finished by Monday Brady, I don't have time to go to the party." 

Even before the last words were out of his mouth, Sam knew he wasn't going to win this one. He had been pushing off every party since he came to Stanford. Brady wasn’t going to let him ditch this one too, he had put too much effort in wearing Sam down to let him stay in their shared dorm.  Looking up from his computer screen Sam sighed at the look on Brady’s face, no he was not getting out of this. 

"Come  _on_  man, you need to get out there... plus there’s this really hot girl I want to introduce you to."

"If she's so hot why aren’t  _you_ asking her out?"

"I did, apparently I'm not her type."

Sam couldn’t hold back his grin, Brady had tried setting him up before, saying it would do Sam good to get laid. Normally it was with girls Brady had already slept with. This was the first time Brady had tried to set him up with someone who turned him down. Shutting off his computer, Sam stood and stretched, thankfully he had about an hour before anyone would show up at the party. Brady must have seen something in his expression as he grinned before clapping Sam on the back. 

"Awesome, go grab a shower, and no flannel, Winchester!"

Seeing that he didn’t have any way out, Sam grabbed his clothes before making his way to the showers. Not having their own shower, they had to use the communal shower for the floor, Sam just hoped that he would have the room to himself. While he was no prude, Sam didn’t enjoy being naked in front of people. Even when he had been hunting with his family Sam tended to dress either in the bathroom, or under his towel, which earned him a lot of Samantha jokes from his brother. Peeking inside the room Sam smiled at the empty space before he stripped down and set up in one of the stalls. There was just enough room for him to fit under the showerhead, although if he grew any taller he would have to duck to make it work. 

Scrubbing with the cheap all-in-one soap mounted to the wall, Sam wondered if he should try finding someone tonight. It wasn’t the first time Brady had mentioned this girl, Jess. From what Sam could tell she seemed his type; blond, smart and sassy. Brady wasn't the only guy she had turned down though, more than one hadn't met the cut from what he heard. While she wasn't a scholarship kid, she spent most of her time in the library or in study hall, dedicated to her classes and seemed perfect. Sadly, Sam knew he couldn't afford to get caught up in perfect, not with his history. It had been a year since he left his family behind, since he ran away, and while he never looked back, eventually his past would catch him. He couldn't afford to get someone else mixed up in his family, not until he was certain they wouldn’t come looking for him. 

It may have been a year, but Sam knew that wasn’t enough time. Maybe once he graduated, when he had his diploma and proved that he could make it on his own in his vanilla life, he could settle down with a nice girl. Until then maybe he could find someone to spend a couple hours with, it wouldn't kill him to let loose and have fun every now and then, even if it was only for a little while. Finishing his shower and changing into a button up and jeans, Sam was ready to at least get a few beers into him and relax. Grabbing his wallet, Sam made his way downstairs to walk to the party with Brady, thankfully it was a nice out and the walk wasn’t too far. They talked on the way there about stupid things, how their classes were going and the latest movie out. Sam realized then that he hadn't been a good friend, he had ignored Brady more than once to study, and while the other student understood, it was still a bad call. 

Sam could easily tell when they were getting close to the party, it would have been hard to miss the loud music and half-trashed people outside. It seemed the party had started early, it wasn’t late enough to have that many drunks out on the lawn. Walking inside Sam waved and said hello to people he knew, most of which were from the same classes. Not trusting the red solo cup one girl passed him, Sam pretended to take a drink before putting it down on the window ledge. Excusing himself Sam made his way to one of the coolers and pulled out a fresh beer, opening the cap and taking a long drink. It was times like this he wished he was raised differently, unlike those around him, Sam couldn’t simply let go, he was always on the lookout for an attack. 

Catching a flash of gold out of the corner of his eye, Sam turned towards it before he was blocked by none other than Brady. Smiling at his friend, Sam noticed he wasn’t alone, a bit to his side was a girl whom he could only describe as beautiful. She was exactly like Brady described; blonde, gorgeous, and seemed to have a sassy look to her, if her stance was anything to go by. If he was in another place in his life; Sam might have asked her out, let Brady set them up, but sadly he couldn’t risk it, not yet. 

"Hey man, lost you for a minute but look who I found! Jess this is Sam, Sam, Jess... is that Carrie from law 101 I'll just leave you two alone... hey Carrie!"

Brady was a whirlwind when he wanted to be, and in a blink of an eye was halfway through the crowd. Sam was left standing there with Jess, his resolve wavered for a moment as the girl obviously checked him out, looking from head to toe before taking a step closer. She had her own drink so he couldn’t offer to grab her one, instead she had an almost feral look to her eye as she spoke to him, a hand coming up to her hair to twirl it in her finger. 

“So, Brady was telling me that you’re my type, I thought he was pulling my leg. He’s not exactly known for hooking other people up, you know? I must say though I am far from disappointed.”

“I’m not… listen I’m flattered, but I’m really not looking for anything right now. Brady means well, but I’m really just not looking.”

It didn’t seem to deter her at all, instead she tilted her back just slightly to enhance her breasts and leaned against the wall to show off the curve of her side. For a moment Sam thought about taking her up on her offer, but he didn’t do casual sex. Dean had always been the one who hooked up after a case, never Sam. Sam wanted more than sex, even if his dick was disagreeing with him. This wasn’t a faceless girl from a bar though, he would run into her from time to time. The campus was only so big, and that wasn’t something he wanted to deal with. Maybe Brady was right and they would hit it off, but not here, not now. 

“Gotta say, this party is turning out better than I thought, you kids need anything?”

The voice was like an answer to his prayer, and while he may not know the guy, Sam was more than willing to give him his undivided attention. Turning, Sam looked at his savior. He was older than most of the crowd; probably in his thirties with golden-blond hair and whiskey eyes, he was shorter than Sam, probably five-six or seven. HIs eyes were what captured Sam, made him want to talk to the man, and for a moment he forgot about the girl he was speaking to. How could she matter when he had a god before him? 

“Umm… no?”

While Sam tried not to blush at his stammering, he noticed that the guy didn’t leave, and instead smiled. There was a twinkle in his eye, like he knew a joke he wasn’t telling. Sam blushed as he saw the man look at him much the same way Jess had earlier, only this time Sam welcomed the glaze. He hadn’t been subtitle in checking the guy out, and thanked every angel he knew that he had kept up on his physical training. While he didn’t broadcast it often, Sam knew that he looked good, had spent many hours a week making sure that he was fit and it paid off well. 

“So, what’s your name big boy?”

The guy was leering at him, stepping closer now that Sam was showing interest and Sam only absently noticed when Jess huffed and walked away. Taking a page out of her book Sam stood up a bit straighter, making sure that his arms were on display from having rolled up his sleeves upon entering the house. What had been said earlier sprung to Sam's mind, this must be the guy who was hosting the party, who had opened his home to a bunch of kids drinking and probably trashing his place. Why someone would do that Sam didn’t know, but he was starting to think it could be to pick up on slightly drunk college students. It wasn’t a pleasant thought, until Sam caught the guys eyes again, and  _damn_  if he didn’t want to be the college student the guy picked for the night. 

“Sam, so this is your place?”

The guy shrugged his shoulders, by now he was right in Sam's personal space and Sam wished he could breathe the guy in. There were too many perfumes and colognes for him to pick up on the guys scent, but Sam hoped to remedy soon. 

“One of them, you like it?”

Nodding his head, Sam tried to sound casual but his breathing was growing heavy as the guy was now pressed against him, a smirk on his lips. 

“Yeah, don’t know why you would open it to getting trashed by a bunch of college kids, but it seems like a nice place.”

“Wanna check out the one room they haven’t been able to trash?”

There was a knowing gleam in his eye then, one Sam could get behind. While Sam hadn’t experienced a lot with guys, he knew what he was getting into. Deciding that he wanted this more than he wanted to keep his distance from attachment, Sam grabbed the back of the guys neck and leaned down to slam their lips together. In all honesty; Sam was expecting the guy to give in, Sam was almost a foot taller than him, but instead the guy seemed to take the kiss as a challenge. Pressing against him, the guy tangled his hand in Sam’s hair and  _pulled,_  it was enough to cause Sam to hiss which was followed by the guy biting down ever so slightly on his bottom lip. 

The combination should have caused warning bells in his head, but Sam found himself growing hard as the guy began to  _own_  his mouth. There was teeth and tongue and at one-point Sam was certain he wasn’t going to get his tongue back. They stood there and kissed, hands roaming above the layers of clothes, Sam wanting to feel skin  _now_. A loud whistle from behind him caused Sam to pull away, his lips red and puffed out from the force of the kiss, his breathing was uneven. He was happy to note that the guy wasn’t fairing much better. 

“So wanna check out that room?”

Giving the guy another kiss as an answer, Sam happily grabbed the others' hand so they didn’t get separated in the crowd, and was pulled up the stairs and down a hallway of closed doors. The guy seemed to notice Sam's question as he started to talk. 

“I don’t mind supplying a room or two, upstairs is where most go to hook up, don’t worry my bedroom is restricted.”

When they came to the end of the hallway the guy pulled out a key to unlock the door, and from the sounds Sam could hear from the other rooms it was a good thing he had thought about locking it. Once the door was open, Sam was ushered inside before the door was closed and locked again. Before he could say anything, Sam was pushed towards the king-sized bed, the smaller man not pausing to let Sam think before there was a mouth on his neck. It was hot and wet and caused a moan from Sam's throat as he fell on the bed. Bouncing slightly on the mattress, Sam found hands on his chest, fingers working open the buttons of his shirt while a mouth returned to his neck, sucking and nipping at his skin. 

“Fuck… name?”

It was all Sam could get out before another moan was pulled from him, the guy biting down hard enough bruise at the bottom of Sam's neck. Shirt opened, the guy pushed it out of the way while nipping and sucking at the exposed skin. Sam had just enough thought to pull the guys shirt from where it was tucked into his pants and started to lift it up, wanting to feel skin. Cold air hit Sam's skin as the warm body was removed, Sam choked back his protest as the guy pulled off his shirt, tossing it to the floor leaving him half naked. Taking in the sight, Sam couldn’t keep his gaze off the man. 

“Call me whatever you want kid, I’m not fussy.”

There was an edge to his voice, something that warned Sam that there was a  _reason_  he wasn’t being given a name, but Sam couldn’t care. It didn’t matter what the guy was called, chances were Sam wouldn’t see him again after tonight, still, he needed more. Pulling at his own shirt, Sam slipped it off his shoulders and pulled his undershirt off leaving his chest bare to the others gaze. Not pausing in case he lost his nerve, Sam unbuckled his belt and made short work of getting his jeans down. They snagged on his shoes, which made the guy move to his knees at the side of the bed. Kneeling before him, the guy gave Sam a look of hunger before he helped Sam out of his shoes and tangled mess of pants. Now that he was bare besides his boxers, Sam started to feel nervous. He had done this before, but it still wasn’t something that he did often enough to feel confident in the bedroom. 

“Reach over and grab a condom from the nightstand, will you? Top drawer.”

Nodding his head, Sam leaned over and reached inside the drawer, fumbling until he could grab one of the loose condoms and pulled it out. Sam didn’t bother shutting the drawer pulling out the bottle of lube he had found as well as a few more condoms, placing them on the top of the nightstand for easier access. Passing the guy the first condom Sam hoped that he was getting the right message, because he  _really_  liked what he thought was about to happen. 

“Tell you what big boy, you blow my mind tonight and I’ll give you my name… if you want it you’re going to  _earn_  it. That work for you?”

Before Sam could answer the guy slipped Sam's boxers down enough to shove in a hand and pull out Sam's hardened cock. Gasping, Sam’s head was thrown back as the firm hand gripped him, pumping a few times, to grow accustomed to the length. Sam knew he was big, was proportional enough it had caused problems with lovers before, especially male ones, but this guy didn’t seem phased in the least. Instead of pulling away at the challenge, the man seemed to be eager for it. 

“I guess my nickname for you is more of a description, big boy indeed. Now rules of the bedroom are; if you don’t like something, you tell me… and try not to use the Lords name in vain, alright?”

“Wha…?”

In what must have been a well-practiced move the guy had the condom open, Sam's cock covered, and a hot mouth was taking Sam in. A sound came from Sam's throat, not quite a moan and not quite a gasp, but something he had never heard himself make before. Sam didn’t have time to think before a wet tongue started licking up his shaft, soft lips pressing against him from time. 

“Fuck…”

Once again, Sam was cut off, this time letting loose a scream as he was unexpectedly all the way inside the guys throat. Others had tried, some even managing to take him; but never this quickly, they always needed to work up to it. Unable to help himself, Sam brought a hand to the guys' head and tangled his fingers in golden hair while the throat around him swallowed. Feeling the man pull back slightly, Sam loosened his grip as the guy set a rhythm, constantly taking Sam down his throat and swallowing before pulling away enough to catch his breath and lick under the head of Sam’s cock before returning. It was enough to drive Sam insane, before too long Sam was whimpering and panting while trusting his hips in time with the guys movements. As the man pulled back, Sam tightened his hand on the guys hair, wanting to thrust back into that hot mouth, he had been so  _close_. 

“Don’t worry, just gotta know if you wanna take the edge off before we get to the main event or hold off? How much did you have to drink, kid?”

It was a legitimate question, but all he could think about was having those lips wrapped around his cock again. 

“Half a beer, I’ll be good to go again… just… I need…”

Sam didn’t need to finish his sentence as he was once again swallowed down. They continued where they had left off, Sam growing more and more impatient. The guy didn’t seem to mind as Sam began to thrust, if anything he moaned at the rough treatment which lead Sam to hold the man's head steady and fuck his mouth. It didn’t take long before Sam was coming, his moans echoing in the room while he held the head of his lover on his cock. When he managed to get his breath back, Sam untangled his hand from the guys hair and was about to stutter an apology when he was met with a grin from the other man, who was discarding the used condom.

“Get in the middle of the bed, I’m not done with you yet big boy.”

Nodding his head, Sam made his way to the middle of the bed, pulling his boxers off his legs while he moved. Once he was laying down on his back Sam turned to look at the man who had him completely blissed out in a matter of minutes. The guy was taking off the rest of his clothes, Sam couldn’t help but be surprised at the others cock. While he wasn’t the thickest Sam had ever seen, he was one of the overall largest. It should have caused Sam to want to put the brakes on the whole thing, he had bottomed before, but it was going to  _hurt_. Still, Sam found himself spreading his legs in invitation. 

“Like I said, you don’t like something, tell me to stop and I will.”

“Sure… it’s been a while though…”

The guy was crawling over him now, their skin pressing together causing short circuits in Sam's brain. Feeling a hand against his chest, slowly rubbing with no real destination, Sam began to calm down.

“I promise, I have no intentions of breaking you tonight… just relax and let me make you feel good.”

Fingers trailed down Sam's chest, stopping to flick and then pinch his nipples before continuing down. The guy was soon nuzzling his neck again, making sure to keep his touches light, mindful of the bruises from his earlier treatment. Once the hand which had been trailing down reached Sam's crotch, it slipped past and started to stroke around Sam's balls, massaging them. While he was still sensitive Sam spread his legs, allowing the guy to fall between them, Sam’s flaccid cock rubbing against a hardened one. Gasping at the sensation, Sam felt his own dick try to harden, slowly becoming interested. 

Fingers that had been playing with his balls moved, slipping behind his balls to play along his arse. When the fingers were removed and the guy sat up, Sam wrapped his legs around him, making sure he didn’t leave before Sam got what he wanted. Hearing a chuckle above him, Sam opened his eyes he didn’t remember closing, and looked at the man who reached over for the lube and condom. Leaning down Sam smiled against the lips pressing on his, the man wasn’t leaving, he was getting the supplies. Instead of returning to their previous position the guy leaned back and helped Sam move one of his legs over the guys shoulder. It left Sam open and exposed, easy access for the man to slip now lubed fingers back to his arse. 

A cold finger rubbed against Sam's rim, testing while spreading lube around his hole to help ease the way. Keeping his movements slow the guy pressed the first finger inside, Sam could feel his gaze, making sure that he was okay while pressing a finger fully inside him. While it was only one finger, Sam knew he was going to be sore tomorrow. He could feel the burn, and while Sam was enjoying the attention, there would be far more needed for him to take the guys cock. Keeping his movements slow the guy twisted his finger slightly, moving it around inside Sam before pulling it out and pushing back in. Sam eventually felt the burn ease before another finger was added to the mix, this one easily reaching that spot inside him that caused Sam to arch his back with a moan. 

“There we go, it’ll only get better from here Sammy.”

Sam grabbed at the sheets under him while the two fingers began to work him open. The guy was tender, making sure not to hurt him, but there was more movement now, more lube added and the twisting had turned to Sam's prostate. As a third finger was added into their play, Sam winced slightly before a lubed hand stroked his half-hard cock. The dual sensations allowed Sam to relax while he was worked open, gasping and panting while the guy made certain Sam was ready for him. 

“Just one more Baby, I need to make sure I won’t hurt you, can you take another for me?”

Nodding his head franticly, a fourth finger was added which caused another hiss from Sam's lips. The guy was quick to press against his prostate, rubbing softly to help with the pain while the hand on Sam's cock pumped. It took several minutes before Sam felt comfortable with four fingers inside him, once he started rocking back into them the guy pulled them away. The sound of a condom wrapper stopped Sam's protest, and Sam went willingly as the guy lifted his other leg over his shoulder. It would have been more comfortable with something under his hips, but Sam wasn’t complaining as he  _finally_  felt the blunt head of the others’ cock against his entrance. Lifting his hips, Sam felt the burn while the other slowly entered him, making sure to keep his movements constant and smooth before bottoming out. 

“Fuck kid, so fucking hot and tight… just let me know…  _fuck_  let me know when.”

The man's voice was wrecked, deeper than before and it ignited something in Sam at having done that to him. Sam had been so focused on his own pleasure he hadn’t considered how the guy was feeling. It seemed that he didn’t have to worry, as he opened his eyes Sam locked gazes with whiskey ones above him. There was pure lust in the others gaze, his pupils blown wide while he waited for Sam to give the okay to move. Instead of answering verbally, Sam pushed against him, circling his hips before nodding his head. It burned, but it was well worth it as the guy leaned back and changed the angle just enough to brush against his sweet spot. 

“There Sammy? Fuck you look so good like this, wanting my cock to fuck that tight ass of yours…”

This time he didn’t wait for a response before pulling out almost completely, hands gripping Sam's hips before slamming back in. Not expecting the force of the thrust, Sam groaned, moving a hand to press against the headboard as he felt them move up the bed. Sam only had a split second to think before he was once again filled with the guys cock. There was no pause, only the hard cock constantly pounding into him, brushing against his prostate every few thrusts while Sam tried to keep breathing. At first, Sam had tried to meet him, but soon found that he couldn’t keep up to the man who was fucking him animalistically. 

“That’s it… such a good boy letting me take you like this… so fucking good for me…”

As the guy stopped, Sam wondered why for a moment before he was lifted, arms around his back pulling Sam up. Quickly Sam moved his arms around the guys neck to help keep his balance while he was lifted and then slammed down. The new position almost made Sam cum, his prostate being slammed into, but it was more than that, Sam  _never_  had a lover who could manhandle him like this. It took a great deal of strength to hold him, and if that wasn’t a massive turn on he didn’t know what was. The guy was panting, his harsh breath tickling Sam's chest where he was licking and nipping. His hips didn’t stop moving, his lover fucking Sam hard and fast while keeping them upright. 

“So so good for me… so fucking tight… I want you to come like this… all filled up with my cock… can you do that for me? Can you come with only my cock?”

The question was panted against his chest, lips fluttering against Sam's nipple while he spoke and causing another moan to rip from Sam's throat while he was lifted and slammed back down. Yes, he could come like this, with nothing touching his cock just being filled by the other. “Yes… yes please…” Sam managed to whimper, his answer making the man even hotter as the grip on Sam's hips flexed before he sped up. Sam was close, his orgasm building, it wouldn’t take much to throw him over the edge. He so desperately wanted to come, wanted to let the sensation wash over him, but he needed  _something_  just a push. 

“Almost there, Baby… you’ve been so good for me… so fucking good… you ready?” As soon as Sam nodded his head the guy tilted ever so slightly and slammed them together, cock pressing against Sam's prostate while the other bit down on the nipple he had been mouthing. The sensation was just enough and Sam screamed as he came, thick ropes of cum splattering between the two of them. Distantly Sam could hear the guy as he continued to slam into him, Sam’s mind elsewhere while he was used for the others pleasure. 

“Yes…  _fuck_  yes… so fucking  _perfect_ …  _fuck_!” Hips stuttered as he came, and while the latex stopped Sam from feeling the cum, he could feel the rush of warmth. The guy held him there for a moment, hips still thrusting while milking his orgasm, but Sam let the afterglow fall over him. Sam didn’t fully come back to himself until after the guy laid him down on the bed, a naked, flaccid cock pressed against his cleaned stomach while the guy snuggled against him. It was such a drastic change from his earlier behavior that it took Sam a minute to register. 

Sam was on his back; the guy snuggled against his side, the two of them still naked, but it was warm enough in the house that he didn’t mind the lack of clothing. Sam wrapped an arm around the guy who now had his head pillowed against Sam's chest, an arm wrapped around his waist. Soft kisses were being planted along his chest, the hand wrapped around Sam's side stroking softly. Letting his own hand rest against the guy, Sam allowed himself to relax in the moment. He didn’t have to think too hard about this, lots of people enjoyed being close after sex, it was comforting. 

“Gabriel.”

Shaking himself out of his thoughts, Sam paused in his light movements. It took a minute for the name to make sense before he smiled, resuming his stroking down the guy-Gabriel’s side. “So, I guess this means I earned it?” The question was in jest, Sam’s mouth running away with him while he relaxed. It had been too long since a warm body was resting against his own, it was something Sam had always enjoyed and he wasn’t about to stop until Gabriel made him. 

“Yeah, I think you earned it… I haven’t come that hard in a long time, Kiddo. Think you wanna earn my last name in the morning?”

Once again Sam found himself pausing. This was exactly why he didn’t try with Jess, he wasn’t ready for a relationship. This was supposed to be a one-night stand, a few hours fun and then he would leave and never see the guy again. It was supposed to be easy, but if anything, it was  _too_  easy with Gabriel. He had managed to press all his buttons, even ones Sam didn’t know he  _had_  and that was something he didn’t want to give up. Feeling the body against his own begin to tense, Sam made a rash decision. It would probably come back to bite him in the ass, but he didn’t want to give this guy up, not now that he knew what he was missing. 

“Yeah, though you might have to feed me after.” Sam could feel Gabriel relax against him, his face nuzzling happily with Sam's response. Sam used his longer legs to kick the blanket, which was folded at the foot of the bed, to wrap around them. Closing his eyes, Sam let himself drift off, a smile on his face while Gabriel remained at his side, a reassuring warmth. Just before he drifted to sleep Sam heard a soft whisper from the Gabriel. “It’s a date.” And yeah, he was okay with that, he would remember to thank Brady tomorrow. 

 

**Author's Note:**

> P.S. If you want to keep up to date on my writing add me to Facebook, Tumbler or Twitter as CrowNoYami ;-) Also, if you want to see what I’m reading (I always review so you know what you’re getting into) I’m on Goodreads as well, same name as always.


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